Last summer, I got an email from my friend Wil, asking me if I wanted to join him in playing the latest version of Dungeons and Dragons. Wil and I have known each other for a few years through my friends Russ and Liz. Wil lives in Minnesota, and he had an interesting proposition – he would lead a team of first-timers through the game as our Dungeon Master (DM), all via Skype and a service called Roll20.net, which basically acts as the virtual version of the mythical Table in Your Parents’ Basement that these games are supposed to be played on.

Olli Jokinen loves his waffles.

I of course said yes, after years of wanting to play and not having the life skills to actually get it together. Because talking to people about my D&D character is about as exciting for non-players as me talking about my fantasy hockey team (his name is Ardbeg Uigeadail, he is named after a whiskey, and he is a Chaotic Good Paladin, thank you for asking. Also my team is called Olli’s Blue Waffles and I am fifth in my league) I’m not going to talk about what’s happening in the game, but there’s some interesting stuff that happens because of the game that is fascinating.

People who haven’t played D&D and think of it as some weird nerdy niche thing – you’re right. It is. But it’s pretty fun and it asks questions of you as a gamer that are challenging to answer (questions like “If I drink while playing via Skype, does that qualify as drinking alone” – the answer is yes it does, but only like 15% alone).

Here are some things that’s I’ve learned from playing D&D that I think are kinda cool.

D&D is The Godfather of modern gaming.

Ardbeg in his natural environment.

Growing up watching The Simpsons and basically every spoof movie made between 1986 and 1999, I had no idea how many references were to classic films like The Godfather and Citizen Kane. D&D plays much the same role in modern gaming, containing so many of the elements (variable damage, turn-based strategy, class-based character design) that make up the video games I love to play.

This is part of what makes the game so interesting – it’s a mitigated process through Wil, but our group is comprised of people who have different signifiers depending on what games and culture they have consumed prior to play. Many of us understand the basic language behind the game because we have effectively reverse-engineered it out of other games, but like any translation there are interpretations that are pulled out by the listener.

D&D will not drive you to Satanism, but it will drive you to homicidal thoughts (about your friends).

Let’s say one of your friends is playing a dwarf who has a couple of interesting character traits; for instance he seems to hate a number of other races (elves in particular) and he seeks to die an honorable death in combat. This leads to a number of complications:

Every single opportunity to charge headfirst into battle, he does so, complicating virtually everyone else’s strategy and plan of attack

His wife is playing an elf, which leads to at least one moment every night where the role playing looks less like medieval fantasy and more like a reality television version of Who’s Afraid of Virginia Woolf?

This part of the game is fantastic, as the blend of role playing with your knowledge of your friends’ innate characteristics creates a hilariously fraught dynamic where people are constantly slipping masks on and off, trying to figure out if comments and actions are in-game or not. The constant fourth-wall breaking and the endless negotiation makes for an experience that is closer to a brainstorming session than a pure play experience.

Our party in action.

D&D is designed to defy expectations while training you in flexibility.

The universal truth of a game predicated on dice rolls is that it is random. The chaos inherent in having to pray to the Random Number God every time you want to do something (with results ranging from – say – leaping across a surging stream, decapitating a goblin archer, to tripping over your own feet, landing facedown in the water and stabbing yourself with your own dagger while the goblins laugh at you) lends every interaction and roll with a sense of real risk and reward.

Consequently, decision-making begins to synthesize two occasionally binary concepts – the actions your character would take in-game, based on your character’s biography and inherent characteristics, and the tantalizing possibility of great success or failure. Because you are relying on randomness to determine outcomes, you have to be able to cope with whatever outcome is presented to you, and decide in the moment what your character should do. You are constantly off-balance, very rarely sure of the outcome, and because the game isn’t iterative – it tells a single narrative that is unbroken no matter what actions take place – you don’t have the luxury of a re-do.

This is the fun thing about the game – you get better at playing the game not by winning, but by better understanding the game’s inherent mechanics. The game is the most fun when characters (and the game’s Dungeon Master) are all adjusting on the fly. Winning this game is less about killing the goblins or collecting the loot, it’s about creating an unbroken string of actions that exist within the game’s narrative, allowing your party to simultaneously imagine and create, like seven people weaving a tapestry whose pattern isn’t dictated by any one of them.

In terms of what else I’ve learned, there’s lots. Being the DM for a game looks extraordinarily hard, but also really, really fun. Also, my character is allergic to arrows. It’s a great way to cement relationships with your friends, share experiences – and lots of laughs).

Regardless of all of that, I know for sure is that I’m looking forward to our next night, sitting by the glow of the screen, in the baleful gaze of the iMac’s webcam. Maybe I’ll have a glass of Ardbeg to celebrate.